title: Total synthesis of (+)-lysergic acid.
abstract: We report the enantioselective total synthesis of (+)-lysergic acid using two different strategies, which featured three metal-catalyzed reactions for the construction of the BCD three rings, involving Pd-catalyzed indole synthesis for the construction of the B ring, a ring-closing metathesis reaction for the formation of the D ring, and an intramolecular Heck reaction to forge the C ring. In synthetic strategy I, the synthesis was achieved in 20 steps following the ring construction sequence of BDC. In synthetic strategy II, the synthetic route was shortened to only 12 steps by following the ring construction sequence of DBC and using a 4-chlorotryptophan derivative for the intramolecular Heck reaction. Moreover, we also discussed an unsuccessful synthetic strategy.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , 38 Xueyuan Road, Beijing 100191, China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Liu
authors.forename: Yu-An
authors.initials: YA
authors.lastname: Zhang
authors.forename: Ping
authors.initials: P
authors.lastname: Xu
authors.forename: Yanxing
authors.initials: Y
authors.lastname: Jia
mesh_terms: D003500:Cyclization; D008237:Lysergic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D008237:Lysergic Acid